Enterprise SaaS Sales Leader Remote

Hybrid or Remote (Secure Engage – Canada/US)

Type

Full Time

Own the full sales cycle for enterprise clients across Canada—prospecting, pitching, negotiating, and closing

Build relationships with compliance, legal, procurement, and risk teams within financial institutions and regulated sectors

Understand client pain points around third-party risk, regulatory pressures, and cybersecurity—and translate these into tailored solutions using Secure Engage’s platform

Drive platform adoption and expand client accounts through cross-sell and upsell opportunities

Maintain accurate pipeline tracking and forecasting in CRM

Partner with product and customer success teams to ensure client satisfaction and identify opportunities for product feedback

5+ years of experience in enterprise B2B SaaS sales, ideally in compliance, security, or legaltech

Demonstrated ability to sell into complex enterprise environments, including banks, insurers, and large law firms

Deep understanding of sales processes, pipeline management, and value-based selling

Strong presentation, negotiation, and relationship-building skills

Experience navigating Canadian regulatory environments is a plus

Self-starter with startup grit—able to thrive in a high-growth, dynamic environment

Remote-first with flexibility to meet enterprise clients in person across Canada

Competitive base salary, commission, and equity options

Paid time off and flexible scheduling

Opportunity to help shape the future of cybersecurity compliance

Collaborative team culture with real impact on product and strategy

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Current Openings

Full-time

Hybrid or Remote (Secure Engage – Canada/US)

Manage and grow relationships with compliance groups in financial institutions
Drive sales and partnership opportunities

Hybrid or Remote (Secure Engage – Canada/US)

Lead the development and execution of Secure Engage’s compliance strategy across North American and international regulatory frameworks (OSFI B-10, DORA, OCC, etc.)

Collaborate with product, engineering, and legal teams to ensure platform readiness and defensibility against financial regulatory standards

Hybrid or Remote (Secure Engage – Canada/US)

Own and execute the overall sales and go-to-market strategy for Secure Engage across North America

Build and lead a high-performance sales team focused on enterprise clients (banks, insurers, law firms, regulators)

Hybrid or Remote (Secure Engage – Canada/US)

Lead the post-sale customer journey—from onboarding to renewal—ensuring enterprise clients receive measurable value from the Secure Engage platform

Build and maintain strong relationships with compliance, legal, and procurement stakeholders at financial institutions and their HRHT third parties

Hybrid or Remote (Secure Engage – Canada/US)

Lead Secure Engage’s fundraising strategy, including preparation of investor materials, pitch support, and financial due diligence

Manage the end-to-end fundraising process—from pipeline development to deal structuring and closing

Hybrid or Remote (Secure Engage – Canada/US)

Own and lead Secure Engage’s global marketing strategy, with a focus on demand generation, brand awareness, and thought leadership in the compliance, legaltech, and cybersecurity space

Build a strong digital and content marketing engine, with clear messaging tailored to CCOs, CISOs, GCs, and regulatory stakeholders in financial institutions and HRHT sectors

Hybrid or Remote (Secure Engage – Canada/US)

• Act as the technical bridge between Sales, Product, and prospective clients—translating complex platform capabilities into clear, compelling value propositions

• Support the sales team during discovery, demos, and technical evaluations with banks, insurers, and law firms

Hybrid or Remote (Secure Engage – Canada/US)

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